Polyamines are known to react with alkylene carbonates to form 2-hydroxyalkyl carbamates. This reaction occurs by merely heating the two reactants at 100.degree. C. (See, for example, U.S. Pat. Nos. 4,122,068; 4,122,069; 4,484,994; and EPO application 0,280,815).
Products containing amino terminal groups and polyether and urea moieties in their backbone have long been known. One method for preparing amino-terminal polyethers having urea groups involves the following reactions of urea with diamines ##STR1## wherein R is a polyether diradical (U.S. Pat. Nos. 4,002,598; 4,115,360: 4,116,938: 4,178,427 and DE 2,748,705). Such materials have been used in combination with aldehydes as epoxy curing agents.
By slightly changing the stoichiometry of the reactants, products have been made containing urea end groups and polyether and urea groups in their backbone such as ##STR2## (U.S. Pat. Nos. 4,141,855 and 4,356,275). Such products have been used in combination with aldehydes as epoxy curing agents.
A second known method of producing amino-terminal polyethers containing urea moieties in their backbone involves the reaction of polyether polyamines with diphenyl carbonate with the removal of phenol as follows: ##STR3## (U.S. Pat. Nos. 4,002,598; 4,115,360; and 4,178,427; N. Yamazaki and S. Nakahams, "Polymer Preprints", ACS, Div. Polym. Chem., 20:146 (1979)).
Yet another process has been described for making products of the same general structure by reacting polyether polyamines with phosgene in the following manner (U.S. Pat. Nos. 4,002,598: 4,115,360 and 4,178,427) ##STR4## These products have also been used as epoxy curing agents.
Products related thereto have also been made by reacting amino alcohols with phosgene (C. Giori, "Polymer Preprints", Acs, Div. Polym. Chem., 11:326 ((1970)).
Still another process for making materials of this type has been reported involving the reaction of polyamines with carbon dioxide in the presence of diphenyl phosphite and pyridine. This process is believed to occur according to the following chemical reaction. ##STR5## Yamazaki, F. Higashi and T. Iguchi, Tetrahedron Letters, 1191 (1974); N. Yamazaki, F. Higashi and T. Iguchi, Tetrahedron, 31:3031 (1975); N. Yamazaki, F. Higashi and T. Iguchi, J. Polym. Sci., Polym. Lett. Ed., 12:517 (1974); and N. Yamazaki, F. Higashi and T. Iguchi, Polym. Ed., 13:785 (1975)).
Polymers have been prepared by reacting alkylene carbonates with hexamethylenediamine at high temperatures. (G. Cameresi, S. Fumasoni, M. Palazzo and F. Pochetti, Ann. Chim. (Rome), 57:927 (1967)). However, the solid polymers prepared by this process are not suitable for use in reaction injection molding processes.
Secondary amines have been reacted with ethylene carbonate to form the corresponding 2-hydroxyethyl carbamate, followed by reaction with alkylene oxides to form the corresponding poly(alkyleneoxy) derivatives (U.S. Pat. No. 4,111,920). Hydroxyalkyl carbamates have been used with epoxy resins for cathodic electrodeposition (U.S. Pat. No. 4,484,994).
Aminated poly(alkylene glycols) have been reacted with alkylene carbonates to produce polyether dicarbamates useful as components in epoxy resins (U.S. Pat. Nos. 4,122,068 and 4,122,069). Materials of this type have been used as polyols and reacted with polyisocyanates to form cellular and non-cellular polyurethanes (U.S. Pat. No. 4,704,446).